# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1009050'
_audit_update_record             
;
2014-06-18 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H76 N12 O20'
_chemical_formula_weight         1381.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0673(14)
_cell_length_b                   14.647(3)
_cell_length_c                   15.480(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1602.4(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9040
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6579
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2696
_reflns_number_gt                2660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxl
_computing_publication_material  'Shelxl and Mercury'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.4672P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_number_reflns         2696
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2447(2) 0.28172(10) 0.03068(9) 0.0299(3) Uani 1 1 d . . .
O2 O 1.0284(2) 0.24953(8) 0.13260(8) 0.0226(3) Uani 1 1 d . . .
O3 O 0.63617(17) 0.53858(8) -0.02523(8) 0.0205(3) Uani 1 1 d . . .
O4 O 1.10471(19) 0.70525(9) -0.05667(9) 0.0257(3) Uani 1 1 d . . .
O5 O 0.9020(2) 0.79443(9) -0.12006(9) 0.0307(3) Uani 1 1 d . . .
N1 N 1.2216(2) 0.46786(11) 0.07277(10) 0.0226(3) Uani 1 1 d . . .
H22 H 1.3422 0.4630 0.0786 0.027 Uiso 1 1 calc R . .
N2 N 0.5111(2) 0.59558(10) -0.07416(10) 0.0221(3) Uani 1 1 d . . .
H2A H 0.4662 0.5652 -0.1204 0.026 Uiso 1 1 calc R . .
H2B H 0.4127 0.6136 -0.0414 0.026 Uiso 1 1 calc R . .
N3 N 0.9426(2) 0.72253(10) -0.08219(9) 0.0213(3) Uani 1 1 d . . .
C1 C 0.6328(3) 0.35877(13) 0.15388(12) 0.0218(4) Uani 1 1 d . . .
H1 H 0.6531 0.3062 0.1215 0.026 Uiso 1 1 calc R . .
C2 C 0.4995(3) 0.35803(14) 0.21980(12) 0.0251(4) Uani 1 1 d . . .
H2 H 0.4337 0.3047 0.2323 0.030 Uiso 1 1 calc R . .
C3 C 0.4643(3) 0.43643(15) 0.26689(12) 0.0268(4) Uani 1 1 d . . .
H3 H 0.3756 0.4358 0.3113 0.032 Uiso 1 1 calc R . .
C4 C 0.5616(3) 0.51590(15) 0.24774(12) 0.0295(4) Uani 1 1 d . . .
H4A H 0.5357 0.5691 0.2783 0.035 Uiso 1 1 calc R . .
C5 C 0.6980(3) 0.51651(14) 0.18293(12) 0.0266(4) Uani 1 1 d . . .
H5A H 0.7640 0.5700 0.1709 0.032 Uiso 1 1 calc R . .
C6 C 0.7364(3) 0.43747(12) 0.13585(11) 0.0190(4) Uani 1 1 d . . .
C7 C 1.0864(3) 0.40318(12) 0.10842(11) 0.0194(4) Uani 1 1 d . . .
H7 H 1.0818 0.4096 0.1714 0.023 Uiso 1 1 calc R . .
C8 C 1.1331(2) 0.30540(12) 0.08488(11) 0.0193(4) Uani 1 1 d . . .
C9 C 0.8116(3) 0.57619(12) -0.02227(11) 0.0176(4) Uani 1 1 d . . .
C10 C 0.7993(3) 0.65830(12) -0.06808(11) 0.0180(4) Uani 1 1 d . . .
C11 C 0.6100(3) 0.66519(12) -0.09833(11) 0.0201(4) Uani 1 1 d . . .
C12 C 0.5195(3) 0.73661(13) -0.15270(12) 0.0266(4) Uani 1 1 d . . .
H12A H 0.3888 0.7215 -0.1616 0.040 Uiso 1 1 calc R . .
H12B H 0.5829 0.7398 -0.2075 0.040 Uiso 1 1 calc R . .
H12C H 0.5285 0.7946 -0.1241 0.040 Uiso 1 1 calc R . .
C13 C 0.8912(3) 0.43391(11) 0.06806(11) 0.0176(4) Uani 1 1 d . . .
H13 H 0.8548 0.3897 0.0235 0.021 Uiso 1 1 calc R . .
C14 C 0.9448(3) 0.52398(12) 0.02390(11) 0.0184(4) Uani 1 1 d . . .
C15 C 1.1372(3) 0.53545(12) 0.03009(12) 0.0207(4) Uani 1 1 d . . .
H15 H 1.2016 0.5851 0.0070 0.025 Uiso 1 1 calc R . .
C16 C 1.0402(3) 0.15203(12) 0.11294(12) 0.0250(4) Uani 1 1 d . . .
H16A H 1.1597 0.1273 0.1330 0.030 Uiso 1 1 calc R . .
H16B H 1.0308 0.1421 0.0511 0.030 Uiso 1 1 calc R . .
C17 C 0.8786(4) 0.10702(14) 0.15868(15) 0.0409(6) Uani 1 1 d . . .
H17A H 0.8944 0.1138 0.2199 0.061 Uiso 1 1 calc R . .
H17B H 0.8759 0.0433 0.1442 0.061 Uiso 1 1 calc R . .
H17C H 0.7620 0.1351 0.1412 0.061 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.203(2) . ?
O2 C8 1.328(2) . ?
O2 C16 1.463(2) . ?
O3 C9 1.358(2) . ?
O3 N2 1.4325(19) . ?
O4 N3 1.238(2) . ?
O5 N3 1.239(2) . ?
N1 C15 1.331(2) . ?
N1 C7 1.454(2) . ?
N1 H1 0.8600 . ?
N2 C11 1.292(2) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C10 1.399(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5A 0.9300 . ?
C6 C13 1.517(2) . ?
C7 C8 1.514(2) . ?
C7 C13 1.580(2) . ?
C7 H7 0.9800 . ?
C9 C10 1.399(2) . ?
C9 C14 1.408(3) . ?
C10 C11 1.421(3) . ?
C11 C12 1.487(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.533(2) . ?
C13 H13 0.9800 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.497(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C16 117.02(14) . . ?
C9 O3 N2 110.17(13) . . ?
C15 N1 C7 112.22(15) . . ?
C15 N1 H1 123.9 . . ?
C7 N1 H1 123.9 . . ?
C11 N2 O3 106.21(15) . . ?
C11 N2 H2A 110.5 . . ?
O3 N2 H2A 110.5 . . ?
C11 N2 H2B 110.5 . . ?
O3 N2 H2B 110.5 . . ?
H2A N2 H2B 108.7 . . ?
O4 N3 O5 122.62(15) . . ?
O4 N3 C10 118.84(15) . . ?
O5 N3 C10 118.54(16) . . ?
C2 C1 C6 120.65(18) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.18(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.76(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.27(19) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.41(19) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 118.67(17) . . ?
C1 C6 C13 119.27(16) . . ?
C5 C6 C13 122.03(17) . . ?
N1 C7 C8 112.44(15) . . ?
N1 C7 C13 103.77(14) . . ?
C8 C7 C13 111.38(14) . . ?
N1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C13 C7 H7 109.7 . . ?
O1 C8 O2 125.16(17) . . ?
O1 C8 C7 125.70(16) . . ?
O2 C8 C7 109.12(14) . . ?
O3 C9 C10 105.97(15) . . ?
O3 C9 C14 114.04(15) . . ?
C10 C9 C14 139.98(17) . . ?
C9 C10 N3 127.75(17) . . ?
C9 C10 C11 106.65(16) . . ?
N3 C10 C11 125.60(16) . . ?
N2 C11 C10 110.98(16) . . ?
N2 C11 C12 119.10(18) . . ?
C10 C11 C12 129.90(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 C14 117.20(15) . . ?
C6 C13 C7 111.48(14) . . ?
C14 C13 C7 101.86(14) . . ?
C6 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C7 C13 H13 108.6 . . ?
C15 C14 C9 129.13(17) . . ?
C15 C14 C13 108.59(16) . . ?
C9 C14 C13 121.90(15) . . ?
N1 C15 C14 112.79(17) . . ?
N1 C15 H15 123.6 . . ?
C14 C15 H15 123.6 . . ?
O2 C16 C17 106.75(16) . . ?
O2 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.040
